CA2236318C - Melane d'alkyl-aryl-sulfonates de metaux alcalino-terreux, son application comme additif pour huile lubrifiante et procede de preparation - Google Patents
Melane d'alkyl-aryl-sulfonates de metaux alcalino-terreux, son application comme additif pour huile lubrifiante et procede de preparation Download PDFInfo
- Publication number
- CA2236318C CA2236318C CA002236318A CA2236318A CA2236318C CA 2236318 C CA2236318 C CA 2236318C CA 002236318 A CA002236318 A CA 002236318A CA 2236318 A CA2236318 A CA 2236318A CA 2236318 C CA2236318 C CA 2236318C
- Authority
- CA
- Canada
- Prior art keywords
- mixture
- sulphonate
- phenyl
- mono
- linear
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 104
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 25
- 239000000654 additive Substances 0.000 title claims abstract description 22
- 230000000996 additive effect Effects 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title description 4
- 229910052751 metal Inorganic materials 0.000 title description 2
- 239000002184 metal Substances 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 11
- -1 phenyl sulphonate radical Chemical class 0.000 claims description 65
- 229930195733 hydrocarbon Natural products 0.000 claims description 33
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 18
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 18
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 17
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 16
- 150000002430 hydrocarbons Chemical class 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 239000002270 dispersing agent Substances 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- 125000005023 xylyl group Chemical group 0.000 claims description 5
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 154
- 150000001336 alkenes Chemical class 0.000 description 52
- 238000005804 alkylation reaction Methods 0.000 description 46
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 46
- 230000029936 alkylation Effects 0.000 description 27
- 239000004215 Carbon black (E152) Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000004711 α-olefin Substances 0.000 description 20
- 239000003921 oil Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 14
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 13
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 8
- 150000004996 alkyl benzenes Chemical class 0.000 description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 5
- 235000011941 Tilia x europaea Nutrition 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 5
- 239000000920 calcium hydroxide Substances 0.000 description 5
- 235000011116 calcium hydroxide Nutrition 0.000 description 5
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000003442 catalytic alkylation reaction Methods 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 239000004571 lime Substances 0.000 description 5
- 150000005673 monoalkenes Chemical class 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 239000010705 motor oil Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 239000004291 sulphur dioxide Substances 0.000 description 2
- 235000010269 sulphur dioxide Nutrition 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000007669 thermal treatment Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000010710 diesel engine oil Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-O hydroxy(oxo)sulfanium Chemical compound O=[SH+]=O RAHZWNYVWXNFOC-UHFFFAOYSA-O 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Un mélange d'alkyl-aryl-sulfonates alcalino-terreux suralcalinisés comportant: (a) 50 % à 85 % en poids d'un mono-alkyl-phényl-sulfonate à chaîne linéaire en C14-C40 dans lequel la proportion molaire de substituant phényl-sulfonate en position 1 ou 2 est comprise entre 0 et 13 %, et (b) 15 % à 50 % en poids d'un alkyl-aryl-sulfonate lourd, dans lequel le radical aryl est phényl ou non et les chaînes alkyl sont soit deux chaînes alkyles linéaires avec un total d'atomes de carbone de 16 à 40, soit une ou plusieurs chaînes alkyles ramifiées avec en moyenne un total d'atomes de carbone de 15 à 48. Dans la mesure où ces mélanges contiennent moins de 10 % de mono-alkyl-phényl-sulfonate linéaire substitué en position 1 ou 2 de la chaîne alkyle linéaire, ils présentent des propriétés les rendant aptes à leur utilisation comme additif détergent-dispersant pour huiles lubrifiantes.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR96/10833 | 1996-09-05 | ||
| FR9610833A FR2752838B1 (fr) | 1996-09-05 | 1996-09-05 | Melange d'alkyl-aryl-sulfonates de metaux alcalino-terreux, son application comme additif pour huile lubrifiante et procedes de preparation |
| PCT/FR1997/001551 WO1998010044A1 (fr) | 1996-09-05 | 1997-09-03 | Melange d'alkyl-aryl-sulfonates de metaux alcalino-terreux, son application comme additif pour huile lubrifiante et procedes de preparation |
| US09/087,106 US6054419A (en) | 1996-09-05 | 1998-05-29 | Mixture of alkyl-aryl-sulfonates of alkaline earth metals, its application as an additive for lubricating oil, and methods of preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2236318A1 CA2236318A1 (fr) | 1998-03-12 |
| CA2236318C true CA2236318C (fr) | 2009-06-02 |
Family
ID=26232943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002236318A Expired - Fee Related CA2236318C (fr) | 1996-09-05 | 1997-09-03 | Melane d'alkyl-aryl-sulfonates de metaux alcalino-terreux, son application comme additif pour huile lubrifiante et procede de preparation |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6054419A (fr) |
| EP (1) | EP0882116B1 (fr) |
| JP (1) | JP4112622B2 (fr) |
| CA (1) | CA2236318C (fr) |
| DE (1) | DE69708848T2 (fr) |
| FR (1) | FR2752838B1 (fr) |
| WO (1) | WO1998010044A1 (fr) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0976810A1 (fr) * | 1998-07-31 | 2000-02-02 | Chevron Chemical S.A. | Mélange d'alkyl-phenyl-sulfonates de métaux alcalino-terreux, son application comme additif pour huile lubrifiante et procédés de préparation |
| FR2783824B1 (fr) | 1998-09-25 | 2001-01-05 | Chevron Chem Sa | Sulfonates d'alkylaryle faibles surbases et huile de lubrification les contenant |
| DE69908098T2 (de) * | 1999-06-10 | 2004-04-08 | Chevron Chemical S.A. | Erdalkalimetalsulfonate, ihre Verwendung als Schmierölzusatz und Herstellungsmethode |
| US6337310B1 (en) | 2000-06-02 | 2002-01-08 | Chevron Oronite Company Llc | Alkylbenzene from preisomerized NAO usable in LOB and HOB sulfonate |
| US6790813B2 (en) * | 2002-11-21 | 2004-09-14 | Chevron Oronite Company Llc | Oil compositions for improved fuel economy |
| US8618029B2 (en) * | 2003-12-22 | 2013-12-31 | Chevron Oronite S.A. | Overbased detergents for lubricating oil applications |
| US8293698B2 (en) * | 2005-07-20 | 2012-10-23 | Chevron Oronite S.A. | Alkylaryl sulfonate detergent mixture derived from linear olefins |
| US8603956B2 (en) * | 2006-04-12 | 2013-12-10 | Chevron Oronite Company Llc | Super overbased polyalkenyl sulfonate and alkylaryl sulfonate composition and process for making the same |
| US7598414B2 (en) * | 2006-06-01 | 2009-10-06 | Chevron Oronite Company Llc | Method of making a synthetic alkylaryl sulfonate |
| US7495140B2 (en) * | 2006-06-01 | 2009-02-24 | Chevron Cronite Company Llc | Method of making a synthetic alkylaryl compound |
| US20080119378A1 (en) | 2006-11-21 | 2008-05-22 | Chevron Oronite Company Llc | Functional fluids comprising alkyl toluene sulfonates |
| US8362153B2 (en) | 2006-12-15 | 2013-01-29 | Chevron Oronite Company Llc | Polyisobutenyl sulfonates having low polydispersity |
| WO2009017497A2 (fr) * | 2007-07-31 | 2009-02-05 | Chevron Oronite Company Llc | Procédé de fabrication d'un alkylaryl sulfonate synthétique |
| US20090163669A1 (en) * | 2007-12-21 | 2009-06-25 | Chevron Oronite LLC | Method of making a synthetic alkylaryl sulfonate |
| US8148591B2 (en) * | 2007-12-21 | 2012-04-03 | Chevron Oronite Company Llc | Method of making a synthetic alkylaryl compound |
| US8076272B2 (en) * | 2009-11-19 | 2011-12-13 | Chevron Oronite Company Llc | Method of making a synthetic alkylaryl sulfonate |
| US8704006B2 (en) | 2010-12-10 | 2014-04-22 | Chevron Oronite Company Llc | Skewed and middle attached linear chain alkylphenol and method of making the same |
| CN102899132A (zh) * | 2012-10-16 | 2013-01-30 | 锦州惠发天合化学有限公司 | 合成烷基苯磺酸钙型润滑油清净剂及生产工艺 |
| US9200230B2 (en) | 2013-03-01 | 2015-12-01 | VORA Inc. | Lubricating compositions and methods of use thereof |
| US9062271B2 (en) | 2013-10-30 | 2015-06-23 | Chevron Oronite Technology B.V. | Process for preparing an overbased salt of a sulfurized alkyl-substituted hydroxyaromatic composition |
| CA2925755A1 (fr) | 2013-10-31 | 2015-05-07 | Chevron Oronite Company Llc | Procede de preparation d'un compose hydroxyaromatique a substitution alkyle ramifie en position para |
| US9376359B2 (en) | 2013-10-31 | 2016-06-28 | Chevron Oronite Company Llc | Process for preparing a para-linear alkyl-substituted hydroxyaromatic compound |
| FI131404B1 (en) * | 2023-05-31 | 2025-04-04 | Neste Oyj | Multi-purpose oil and method for producing the same |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3764533A (en) * | 1970-08-07 | 1973-10-09 | Continental Oil Co | Oil soluble dialkaryl sulfonate compositions |
| US4298547A (en) * | 1979-07-27 | 1981-11-03 | Mobil Oil Corporation | Preparation of improved alkylphenylsulfonates |
| JP2598489B2 (ja) * | 1987-10-12 | 1997-04-09 | エクソン ケミカル パテンツ インコーポレーテッド | 過塩基マグネシウムスルホン酸塩組成物 |
| GB8723909D0 (en) * | 1987-10-12 | 1987-11-18 | Exxon Chemical Patents Inc | Lubricant oil additive |
| GB8723907D0 (en) * | 1987-10-12 | 1987-11-18 | Exxon Chemical Patents Inc | Overbased metal sulphonate composition |
| CA2051279C (fr) * | 1990-12-31 | 2003-05-27 | Tze-Chi Jao | Sulfonate de calcium avec exces de base |
| EP0645444A3 (fr) * | 1993-09-27 | 1995-05-24 | Texaco Development Corp | Lubrifiants contenant des détergents surbasiques aromatiques ayant des groupes substituants alkyles linéaires. |
-
1996
- 1996-09-05 FR FR9610833A patent/FR2752838B1/fr not_active Expired - Fee Related
-
1997
- 1997-09-03 DE DE69708848T patent/DE69708848T2/de not_active Expired - Lifetime
- 1997-09-03 EP EP97938974A patent/EP0882116B1/fr not_active Expired - Lifetime
- 1997-09-03 JP JP51230398A patent/JP4112622B2/ja not_active Expired - Fee Related
- 1997-09-03 WO PCT/FR1997/001551 patent/WO1998010044A1/fr not_active Ceased
- 1997-09-03 CA CA002236318A patent/CA2236318C/fr not_active Expired - Fee Related
-
1998
- 1998-05-29 US US09/087,106 patent/US6054419A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP4112622B2 (ja) | 2008-07-02 |
| US6054419A (en) | 2000-04-25 |
| EP0882116B1 (fr) | 2001-12-05 |
| FR2752838B1 (fr) | 1998-12-04 |
| DE69708848D1 (de) | 2002-01-17 |
| WO1998010044A1 (fr) | 1998-03-12 |
| DE69708848T2 (de) | 2002-06-20 |
| JPH11514702A (ja) | 1999-12-14 |
| FR2752838A1 (fr) | 1998-03-06 |
| EP0882116A1 (fr) | 1998-12-09 |
| CA2236318A1 (fr) | 1998-03-12 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160906 |